How This AI Startup Grew to $50M ARR in 2 Years (Marketing Playbook)
Want to steal Gamma's influencer-led strategy? Get our 10 AI prompts: https://clickhubspot.com/hgb
Ep. 363
Is influencer marketing the new product virality?
Kipp and Kieran dive into the viral marketing playbook that skyrocketed an AI startup to $50M ARR and 50 million users with just 30 employees. Learn more on the explosive power of influencer-led growth, why building brand outranks traditional performance marketing, and the essential product feedback loops that every modern startup needs to stay ahead in the competitive AI era.
Mentions
Gamma https://gamma.app/
Dropbox https://www.dropbox.com/
Lovable https://lovable.dev/
Anton Osika https://www.linkedin.com/in/antonosika/
Grant Lee https://www.linkedin.com/in/grantslee/
Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt
We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business.
To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research
Resource
[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip
We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed
YouTube: https://www.youtube.com/channel/UCGtXqPiNV8YC0GMUzY-EUFg
Twitter: https://twitter.com/matgpod
TikTok: https://www.tiktok.com/@matgpod
Join our community https://landing.connect.com/matg
Thank you for tuning into Marketing Against The Grain!
Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934
If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends.
We really appreciate your support.
Host Links:
Kipp Bodnar, https://twitter.com/kippbodnar
Kieran Flanagan, https://twitter.com/searchbrat ‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.
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22:04
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22:04
The Brand NEW AI Marketing Strategy for 2025
Want our free Loop Marketing Prompt Library (with 100 prompts)? Get it here: https://clickhubspot.com/kcl
Ep. 362
Did you know that 58.5% of Google searches now end without a click?
Kipp and Aja Frost, Sr. Director of Global Growth at HubSpot, dive into how AI has fundamentally changed the marketing landscape—and what you can do about it. Learn more on why old-school tactics like linear funnels and basic personalization are outdated, how “loop marketing” can future-proof your strategy, and which AI-powered tactics drive explosive growth when traffic and attention are harder than ever to capture. This episode was recorded at HubSpot’s Inbound 2025.
Mentions
HubSpot Inbound https://www.inbound.com/
Aja Frost https://www.linkedin.com/in/ajafrost/
Claude https://claude.ai/
Perplexity https://www.perplexity.ai/
Breeze Assistant https://knowledge.hubspot.com/ai/use-breeze-assistant
Gemini https://gemini.google.com/
Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt
We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business.
To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research
Resource
[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip
We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed
YouTube: https://www.youtube.com/channel/UCGtXqPiNV8YC0GMUzY-EUFg
Twitter: https://twitter.com/matgpod
TikTok: https://www.tiktok.com/@matgpod
Join our community https://landing.connect.com/matg
Thank you for tuning into Marketing Against The Grain!
Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934
If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends.
We really appreciate your support.
Host Links:
Kipp Bodnar, https://twitter.com/kippbodnar
Kieran Flanagan, https://twitter.com/searchbrat
‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.
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32:58
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32:58
This is How the Top 1% Marketers are Using AI
Want 22 ChatGPT Marketing Agents to handle your work? Get it here: https://clickhubspot.com/bpg
Ep. 361
Marketing is only limited by your own creativity and ambition right now.
Kipp and Nicholas Holland, Head of AI, SVP Product at HubSpot, dive into how the world’s top 1% of marketers are deploying AI for explosive growth. Learn more on why context is the most important word for AI in 2026, the rise of agents and assistants for every marketing use case, and how today’s marketers can 10x their creativity by practicing and pushing past the limits of what’s possible.
Mentions
Nicholas Holland https://www.linkedin.com/in/nashvilleholland/
HubSpot Breeze https://www.hubspot.com/products/ai
ChatGPT https://chatgpt.com/
Gemini https://gemini.google.com/
Nano Banana https://nanobanana.ai/
Google Veo https://deepmind.google/models/veo/
Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt
We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business.
To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research
Resource
[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip
We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed
YouTube: https://www.youtube.com/channel/UCGtXqPiNV8YC0GMUzY-EUFg
Twitter: https://twitter.com/matgpod
TikTok: https://www.tiktok.com/@matgpod
Join our community https://landing.connect.com/matg
Thank you for tuning into Marketing Against The Grain!
Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934
If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends.
We really appreciate your support.
Host Links:
Kipp Bodnar, https://twitter.com/kippbodnar
Kieran Flanagan, https://twitter.com/searchbrat ‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.
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26:29
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26:29
I Stole Microsoft CEO’s 4 Most Powerful AI Prompts
Want Kieran's 4 AI prompts that drive big results? Get it here: https://clickhubspot.com/uph
Ep. 360
Did you know the CEO of Microsoft, just gave away his four most powerful daily AI prompts for boosting productivity and leadership?
Kieran dives into how you can swipe, upgrade, and use the very same prompts Satya Nadella relies on every single day. Learn how to prep smarter for every meeting, get real-time project status updates, check if you’ll hit your deadlines, and analyze exactly how you’re spending your time.
Mentions
Satya Nadella https://www.linkedin.com/in/satyanadella/
Microsoft https://www.microsoft.com/en-us/
Microsoft Copilot https://copilot.microsoft.com/chats/HATNMvfutDfR73T3acuz1
Claude https://claude.ai/
Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt
We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business.
To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research
Resource
[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip
We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed
YouTube: https://www.youtube.com/channel/UCGtXqPiNV8YC0GMUzY-EUFg
Twitter: https://twitter.com/matgpod
TikTok: https://www.tiktok.com/@matgpod
Join our community https://landing.connect.com/matg
Thank you for tuning into Marketing Against The Grain!
Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934
If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends.
We really appreciate your support.
Host Links:
Kipp Bodnar, https://twitter.com/kippbodnar
Kieran Flanagan, https://twitter.com/searchbrat
‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.
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15:16
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15:16
Marketing is Broken - This is the Future of Conversions (Loop Framework)
Want our NEW Loop Marketing Prompt Library? Get it here: https://clickhubspot.com/lmp
Ep. 359
Did you know that 60% of Google searches now end without a single click?
Kipp and Aja Frost, Sr. Director of Global Growth at HubSpot, dive into why traditional marketing is broken and what the future of conversions looks like in a world dominated by AI. Learn more about how AI is upending search and website traffic, why the future belongs to marketers who can personalize experiences at scale, and the brand new Loop Framework that will transform how you drive results in 2024 and beyond.
Mentions
Aja Frost https://www.linkedin.com/in/ajafrost/
HubSpot Loop Marketing https://www.hubspot.com/loop-marketing
ChatGPT https://chatgpt.com/
Claude https://claude.ai/
Perplexity https://www.perplexity.ai/
Quora https://www.quora.com/
Reddit https://www.reddit.com/
Discord https://discord.com/
Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt
We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business.
To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research
Resource
[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip
We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed
YouTube: https://www.youtube.com/channel/UCGtXqPiNV8YC0GMUzY-EUFg
Twitter: https://twitter.com/matgpod
TikTok: https://www.tiktok.com/@matgpod
Join our community https://landing.connect.com/matg
Thank you for tuning into Marketing Against The Grain!
Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934
If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends.
We really appreciate your support.
Host Links:
Kipp Bodnar, https://twitter.com/kippbodnar
Kieran Flanagan, https://twitter.com/searchbrat
‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.
Kipp Bodnar (HubSpot’s CMO) and Kieran Flanagan (Hubspot's SVP of Marketing), lead you down the rabbit hole of marketing trends, growth tactics and innovation. On the way you’ll pick up undiscovered strategies to give you that slight edge for success. These are not your typical twitter thread regurgitated marketing tactics that everyone is doing. These are new methods, with unfiltered examination of successful fresh ideas.